Pinacol → Phenylboronic acid pinacol ester

HRID 537596

Reaction equation

HRID 537596 reaction equation
[C:1]1([B:7]([OH:9])[OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O[C:11]([C:14](O)([CH3:16])[CH3:15])([CH3:13])[CH3:12]>C1(C)C=CC=CC=1>[C:1]1([B:7]2[O:9][C:14]([CH3:16])([CH3:15])[C:11]([CH3:13])([CH3:12])[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6425PinacolHCID 66827Phenylboronic Acid

Product 1

HCID 570673Phenylboronic acid pinacol ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

Phenyl boronic acid (100 g, 0.82 mol, 1 equiv.) and pinacol (96.92 g, 0.82 mol, 1 equiv.) were dissolved in toluene (500 mL) at room temperature. The cloudy solution was then placed on to a rotary evaporator and stirred for 2 hours at 60° C. After this period the solid had dissolved, concurrent with the formation of water (ca. 29.5 mL) as a second layer. The water was then removed in a separating funnel and the crude reaction filtered through Celite. Evaporation of the solvent yielded a clear pale yellow oil which solidified on cooling in a refrigerator to give the title compound in a near-quantitative yield as a white solid (ca. 167 g).

Workup

  1. customThe cloudy solution was then placed on to a rotary evaporator
  2. dissolutionAfter this period the solid had dissolved, concurrent with the formation of water (ca. 29.5 mL) as a second layer
  3. customThe water was then removed in a separating funnel
  4. customthe crude reaction
  5. filtrationfiltered through Celite
  6. customEvaporation of the solvent
  7. customyielded a clear pale yellow oil which
  8. temperatureon cooling in a refrigerator

Sources & evidence

ORD record
ord-476333c707844cd7b816acb156eb2f6d
Source dataset
uspto-grants-2014_10
Patent number
US08860007B2

Linked notes

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